SK3202001A3 - Drug and a pharmaceutical composition for treating diabetes, insulin resistance, obesity, hyperglycemia, hyperinsulinemia or increased level - Google Patents
Drug and a pharmaceutical composition for treating diabetes, insulin resistance, obesity, hyperglycemia, hyperinsulinemia or increased level Download PDFInfo
- Publication number
- SK3202001A3 SK3202001A3 SK320-2001A SK3202001A SK3202001A3 SK 3202001 A3 SK3202001 A3 SK 3202001A3 SK 3202001 A SK3202001 A SK 3202001A SK 3202001 A3 SK3202001 A3 SK 3202001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- inhibitor
- derivative
- phenyl
- hydrogen
- Prior art date
Links
- 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims description 29
- 208000008589 Obesity Diseases 0.000 title claims description 24
- 235000020824 obesity Nutrition 0.000 title claims description 24
- 206010022489 Insulin Resistance Diseases 0.000 title claims description 23
- 239000003814 drug Substances 0.000 title claims description 22
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 20
- 201000001421 hyperglycemia Diseases 0.000 title claims description 20
- 206010060378 Hyperinsulinaemia Diseases 0.000 title claims description 18
- 230000003451 hyperinsulinaemic effect Effects 0.000 title claims description 18
- 201000008980 hyperinsulinism Diseases 0.000 title claims description 18
- 229940079593 drug Drugs 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 101001062864 Homo sapiens Fatty acid-binding protein, adipocyte Proteins 0.000 claims abstract description 113
- 102100030431 Fatty acid-binding protein, adipocyte Human genes 0.000 claims abstract description 100
- 239000003112 inhibitor Substances 0.000 claims abstract description 81
- -1 alkyl radical Chemical class 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000003472 antidiabetic agent Substances 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 235000011187 glycerol Nutrition 0.000 claims description 16
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229940125708 antidiabetic agent Drugs 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 102000047030 human FABP4 Human genes 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000539 amino acid group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 102000004877 Insulin Human genes 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229940125396 insulin Drugs 0.000 claims description 8
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 7
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 7
- 108090001061 Insulin Proteins 0.000 claims description 7
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000003230 pyrimidines Chemical class 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- 229960004580 glibenclamide Drugs 0.000 claims description 6
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 102000004366 Glucosidases Human genes 0.000 claims description 5
- 108010056771 Glucosidases Proteins 0.000 claims description 5
- 229940124754 PPAR-alpha/gamma agonist Drugs 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 230000009977 dual effect Effects 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical group CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 5
- 229960003105 metformin Drugs 0.000 claims description 5
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 5
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 229940122355 Insulin sensitizer Drugs 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 235000021588 free fatty acids Nutrition 0.000 claims description 4
- 229950004994 meglitinide Drugs 0.000 claims description 4
- 150000007978 oxazole derivatives Chemical class 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 claims description 4
- 229960001641 troglitazone Drugs 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- CQHYICHMGNSGQH-UHFFFAOYSA-N 1,3-oxazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CO1 CQHYICHMGNSGQH-UHFFFAOYSA-N 0.000 claims description 3
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims description 3
- OSCOEGOIEGAFDI-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)-4-phenyl-1,3-oxazole Chemical class C1=COC(C=2OC=C(N=2)C=2C=CC=CC=2)=N1 OSCOEGOIEGAFDI-UHFFFAOYSA-N 0.000 claims description 3
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical class O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 claims description 3
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 claims description 3
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229960001761 chlorpropamide Drugs 0.000 claims description 3
- 229960000346 gliclazide Drugs 0.000 claims description 3
- 229960004346 glimepiride Drugs 0.000 claims description 3
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 claims description 3
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 claims description 3
- 229960001381 glipizide Drugs 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 claims description 3
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- FTPLHCPJZLDACP-UHFFFAOYSA-N 5,6-dihydrofuro[2,3-d]pyrimidine Chemical compound N1=CN=C2OCCC2=C1 FTPLHCPJZLDACP-UHFFFAOYSA-N 0.000 claims description 2
- NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 claims description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims description 2
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 229960002632 acarbose Drugs 0.000 claims description 2
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000007980 azole derivatives Chemical class 0.000 claims description 2
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 150000004283 biguanides Chemical group 0.000 claims description 2
- 230000036765 blood level Effects 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 229960001110 miglitol Drugs 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
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Classifications
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Endocrinology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10067798P | 1998-09-17 | 1998-09-17 | |
| PCT/US1999/020946 WO2000015229A1 (en) | 1998-09-17 | 1999-09-13 | METHOD FOR TREATING DIABETES EMPLOYING AN aP2 INHIBITOR AND COMBINATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK3202001A3 true SK3202001A3 (en) | 2002-04-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK320-2001A SK3202001A3 (en) | 1998-09-17 | 1999-09-13 | Drug and a pharmaceutical composition for treating diabetes, insulin resistance, obesity, hyperglycemia, hyperinsulinemia or increased level |
Country Status (30)
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| US (1) | US20020035064A1 (cs) |
| EP (2) | EP1121129B1 (cs) |
| JP (2) | JP2002524517A (cs) |
| KR (2) | KR20010079842A (cs) |
| CN (2) | CN1317970A (cs) |
| AT (1) | ATE406898T1 (cs) |
| AU (2) | AU754488B2 (cs) |
| BG (2) | BG105432A (cs) |
| BR (2) | BR9913833A (cs) |
| CA (2) | CA2344300A1 (cs) |
| CO (2) | CO5130026A1 (cs) |
| CZ (2) | CZ2001964A3 (cs) |
| DE (1) | DE69939481D1 (cs) |
| EE (2) | EE04356B1 (cs) |
| ES (1) | ES2311306T3 (cs) |
| GE (2) | GEP20033045B (cs) |
| HU (2) | HUP0104240A2 (cs) |
| ID (2) | ID27833A (cs) |
| IL (2) | IL141786A0 (cs) |
| LT (2) | LT4871B (cs) |
| LV (2) | LV12687B (cs) |
| NO (2) | NO20011352L (cs) |
| NZ (2) | NZ510209A (cs) |
| PE (2) | PE20001047A1 (cs) |
| PL (2) | PL346661A1 (cs) |
| SK (1) | SK3202001A3 (cs) |
| TR (2) | TR200100773T2 (cs) |
| UY (2) | UY25713A1 (cs) |
| WO (2) | WO2000015230A1 (cs) |
| ZA (2) | ZA200207433B (cs) |
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| AU1172999A (en) * | 1997-11-19 | 1999-06-07 | Takeda Chemical Industries Ltd. | Novel apoptosis inhibitors |
| AU2005201289B2 (en) * | 1999-02-12 | 2008-04-17 | President And Fellows Of Harvard College | Inhibiting formation of atherosclerotic lesions |
| DE60041246D1 (de) * | 1999-02-12 | 2009-02-12 | Harvard College | Hemmung der bildung von atherosklerotischen wunden mittels afabp antisens nukleinsäuren |
| US6548529B1 (en) * | 1999-04-05 | 2003-04-15 | Bristol-Myers Squibb Company | Heterocyclic containing biphenyl aP2 inhibitors and method |
| US6586438B2 (en) | 1999-11-03 | 2003-07-01 | Bristol-Myers Squibb Co. | Antidiabetic formulation and method |
| WO2001054694A1 (en) | 2000-01-28 | 2001-08-02 | Bristol-Myers Squibb Company | Tetrahydropyrimidone inhibitors of fatty acid binding protein and method |
| US6670380B2 (en) | 2000-11-20 | 2003-12-30 | Bristol-Myers Squibb Co. | Pyridone inhibitors of fatty acid binding protein and method |
| EP1385549A2 (en) * | 2001-03-12 | 2004-02-04 | Novartis AG | Combination of nateglinide or repaglinide with at least one further antidiabetic compound |
| US6919323B2 (en) | 2001-07-13 | 2005-07-19 | Bristol-Myers Squibb Company | Pyridazinone inhibitors of fatty acid binding protein and method |
| WO2003007888A2 (en) * | 2001-07-20 | 2003-01-30 | Adipogenix, Inc. | Fat accumulation-modulating compounds |
| WO2003043624A1 (en) | 2001-11-16 | 2003-05-30 | Bristol-Myers Squibb Company | Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein |
| AU2004210127B2 (en) | 2003-01-27 | 2009-10-01 | Merck Sharp & Dohme Corp. | Substituted pyrazoles, compositions containing such compounds and methods of use |
| AU2004224825A1 (en) * | 2003-03-26 | 2004-10-07 | Crc For Asthma Limited | Therapeutic and prophylactic compositions and uses therefor |
| WO2004096977A2 (en) * | 2003-04-30 | 2004-11-11 | Pfizer Products Inc. | Crystal structure of homo sapiens adipocyte lipid binding protein and uses thereof |
| PT1725234E (pt) | 2004-03-05 | 2013-03-04 | Univ Pennsylvania | Métodos com efeitos secundários reduzidos para tratamento de patologias ou doenças associadas a hiperlipidemia e hipercolesterolemia |
| MXPA06014084A (es) | 2004-06-04 | 2007-02-15 | Merck & Co Inc | Derivados de pirazol, composiciones que contienen dichos compuestos y metodos de uso. |
| WO2006028970A1 (en) | 2004-09-02 | 2006-03-16 | Cengent Therapeutics, Inc. | Derivatives of thiazole and thiadiazole inhibitors of tyrosine phosphatases |
| WO2006089177A2 (en) | 2005-02-17 | 2006-08-24 | Synta Pharmaceuticals Corp. | Isoxazole combretastin derivatives for the treatment of disorders |
| WO2007015999A2 (en) | 2005-07-26 | 2007-02-08 | Merck & Co., Inc. | Process for synthesizing a substituted pyrazole |
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1999
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- 1999-09-13 EE EEP200100154A patent/EE04356B1/xx not_active IP Right Cessation
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- 1999-09-13 AT AT99951438T patent/ATE406898T1/de not_active IP Right Cessation
- 1999-09-13 JP JP2000569813A patent/JP2002524517A/ja active Pending
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- 1999-09-13 KR KR1020017003408A patent/KR20010079842A/ko not_active Withdrawn
- 1999-09-13 CN CN99811000A patent/CN1317970A/zh active Pending
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- 1999-09-13 AU AU63877/99A patent/AU754488B2/en not_active Ceased
- 1999-09-13 CZ CZ2001964A patent/CZ2001964A3/cs unknown
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- 1999-09-13 WO PCT/US1999/021069 patent/WO2000015230A1/en not_active Application Discontinuation
- 1999-09-13 CA CA002344300A patent/CA2344300A1/en not_active Abandoned
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- 1999-09-13 PL PL99346660A patent/PL346660A1/xx not_active Application Discontinuation
- 1999-09-13 NZ NZ510209A patent/NZ510209A/en unknown
- 1999-09-13 KR KR1020017003411A patent/KR20010075150A/ko not_active Withdrawn
- 1999-09-13 EE EEP200100155A patent/EE200100155A/xx unknown
- 1999-09-13 DE DE69939481T patent/DE69939481D1/de not_active Revoked
- 1999-09-13 NZ NZ510207A patent/NZ510207A/en unknown
- 1999-09-13 EP EP99951438A patent/EP1121129B1/en not_active Revoked
- 1999-09-13 AU AU61437/99A patent/AU755563B2/en not_active Ceased
- 1999-09-13 EP EP99948210A patent/EP1113801A4/en not_active Withdrawn
- 1999-09-13 HU HU0104108A patent/HUP0104108A2/hu unknown
- 1999-09-13 WO PCT/US1999/020946 patent/WO2000015229A1/en not_active Application Discontinuation
- 1999-09-13 CA CA002344309A patent/CA2344309A1/en not_active Abandoned
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2001
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